Sitting on the sofa a while back, I suddenly blurted out to my husband, “I don’t care what anybody says. When I’m 50 years old, I hope I look half as good as Morgan Freeman does today.”
This was met with much laughter, and eventually figuring out that I had meant Fairchild, not Freeman.
A few years ago, I was sitting in a restaurant with a friend, when a waitress we were both good friends with passed by our table and jokingly sneered: “Wench!”
My friend looks up at her, and says, trying to be witty, “You’re close. Just spell it with a ‘B’ and you’ll know what I am.”
I looked up at her, startled. “You’re a bench?”
What are your favourite “aww-crap-you-know-what-I-meant” moments?
• My friend Joe suggested I take up true-crime writing and—in trying to suggest I could become a female version of Dominick Dunne—said, “You could be the next Dominique Dunne!”
• Just last week a friend locked his keys out of his car and we had to call Triple-A. As the Triple-A guy quickly finessed his way into the car, my friend said admiringly, “Wow—you really live up to your Triple-A-ness!”
(say that last one out loud)
Well, I guess I’m as dumb as you, because I don’t know whast else she means. Unless she means bitch, but you don’t get bitch by spelling wench with a ‘b’, so I’m confused. 
I think she meant the general gist of the word, not the exact spelling 
I once innocently said to my friend Butch, that I thought a better name for him would require him just changing one letter of this name. He did not find this amusing and I said (after discovering he was actually born in the Netherlands), “What’s offensive about being called Dutch?” 
I’m just trying to imagine how one would go about living up to that.
I’m glad you put the hint in to say that out loud, because I thought it was a breast cup joke. Where is my mind?
Another word that starts with a “w” that would fit the “b” is “witch”. At least it rhymes.
LilyoftheValley writes:
In Swaziland:
Yep, she meant “bitch”. I should have pointed out, that story was about her dumbness, not mine. I just like to add my reply as the “punchline”, though all I did was point out the obvious. Other friends were in the restaurant and mentioned later that until I said it out loud, they just processed it as “bitch” and snickered, but then I had to go and “zing” her in front of everyone.
So hey, maybe I’m the real bench here.
Another one from me:
My father was telling me about how he loved to make my brother and I solve riddles (and also tell us bad puns!) growing up. He told me he just liked to make sure his kids knew how to think laterally as well as literally in any situation, so we could always think of alternative solutions and not take everything at face value, etc etc etc. A noble enough cause. Then he asks me if I can remember the first riddle he ever asked me. I sighed long-sufferingly and rolled my eyes. How can I forget when he’s always reminding me? I made a circle with my thumb and forefinger and held it near my forehead, then used my other hand to poke my forehead with my finger, and said, “Yeah, yeah. Can you poke your hole through a head this big?”
The poor man laughed 'til he cried.